


Slow Burn

by keefling



Series: Playdates [2]
Category: Critical Role (Web Series)
Genre: Aftercare, Casual Sex, Dom/sub, Flogging, M/M, Oral Sex, Risk Aware Consensual Kink, Safewords, Trans Male Character
Language: English
Status: Completed
Published: 2018-06-20
Updated: 2018-06-20
Packaged: 2019-05-25 17:59:16
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,545
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14982545
Author URL: https://archiveofourown.org/users/keefling/pseuds/keefling
Summary: “I want to play, Mollymauk,” Caleb said with a shy smile, “If you have the time.”  His eyes flickered back and forth between Molly’s face and the floor.“I always have time for you, Caleb,” Molly answered with a smile of his own, “Sit down and tell me what you need.”





	Slow Burn

**Author's Note:**

> This one goes out to Rene for the lovely suggestions and the inspiration to turn this into a series.
> 
> This can be read as a stand-alone fic, but I recommend reading [Prestidigitation](https://archiveofourown.org/works/14926989) first for additional context. 
> 
> Caleb is a trans man in this fic, and I use feminine-coded words to describe his genitals

Caleb was on all fours, naked on the bed with his knees a shoulder width apart.  It was pitch dark; his vision obscured by the silken blindfold that covered his eyes.  He felt Mollymauk’s presence to the right of the bed, but not being able to see him was making Caleb grow anxious in the heavy silence.  He trusted Molly’s word that, above all else, he would not leave Caleb alone.  Molly followed through on that promise, placing a palm on his shoulder to let him know that he was still there, still real, still within Caleb’s reach.

“Posture, Caleb.  Spine straight, knees bend, elbows unlocked.”  Molly’s voice was pleasant, respectful, but it carried the weight of a command.

“Yes, sir,” Caleb said.  He steadied himself, taking deep breaths into his diaphragm, just as Molly had taught him to calm his nerves.

“Good boy,” Molly said, giving his shoulder a reassuring squeeze and dislodging the knot in Caleb’s chest.  “You’re doing great.”

 

* * *

 

It had taken Caleb weeks to figure out what he wanted to do next, and even longer to put it into words.  He had longed to return to the place of inner peace and calm that he had found in Molly’s room that night.  Caleb had wanted to be ready, wanted to make sure he knew what he was going into before he asked Molly to accompany him.  A part of him had even wanted to impress Mollymauk.  So being the studious man that he was, Caleb had done his research.

Molly had begun to worry that Caleb would be too shy to initiate another playdate, so if someone had told him that morning that he would have Caleb on his knees by nightfall, he would have told them that they were crazy.  He was about to begin his nightly ritual when he heard a knock on his door.  He was delighted to find a nervous, fidgeting Caleb standing in the doorway.

“Caleb!  It’s good to see you,” Molly greeted him, thowing an arm over his shoulders and ushering him inside.  “What can I do for you, my dear?”

“I want to play, Mollymauk,” Caleb said with a shy smile.  “If you have the time.” His eyes flickered back and forth between Molly’s face and the floor.

“I always have time for you, Caleb,” Molly answered with a smile of his own.  “Sit down and tell me what you need.”

“I just….ah, I want….I need…” Caleb stuttered, refusing to stand still.  His heart pounded and he tried his best to stave away the impending panic attack that threatened to yank the ground from beneath his feet.  He wrung his hands, scratched at his wrists with bitten-off nails.  He had run the conversation through his head until he had perfected it, but the words fell away and left him treading water in a sea of self-doubt.  Molly saw the fear in Caleb’s eyes and could not bear to watch, so he pried Caleb’s hands apart and held them gently in his own.

“Shh, shh, let me help,” Molly offered, his gentle voice bringing Caleb back into the room.  Caleb’s eyes prickled with tears from a combination of stress and gratitude.  Still holding his hands, Molly sat on the bed so that he was looking up at Caleb instead of down.  “It’s alright.  Take all the time you need.”

“This is….a different kind of request, and you can say no, but I….I want you to hurt me,” Caleb said after a moment.  He swallowed hard.  “I have done some reading and I….I think I would enjoy it.”

“Oh?” Molly’s face lit up, bolstering Caleb’s confidence.  His tail swished behind him, a quiet hiss against the sheets.  “Tell me you weren’t reading one of Jester’s books?”

“Of course not,” Caleb laughed, blushing deep red.  “I am being serious.” He took a deep breath and leaned down until they were at eye level.  “I want you to whip me.  Mark my skin.  Hit me until my ass is red.  Make beg for it, Mollymauk.  You can do this, _ja?_ ”  It was not nearly as eloquent as he had rehearsed, but from the way Molly’s tail thudded excitedly on the mattress, the tiefling did not seem interested in poetry.

”Oh, definitely.  All of that and more,” Molly purred, grinning at Caleb with a hunger that made the wizard take a step back.

“You will do these things to me?” Caleb whispered, disbelieving but hopeful.

“I would love to indulge you,” Molly said, kissing the back of Caleb’s hand.  “So I’m sorry, dear, for what I’m about to ask you.”

Uncomfortable as he was, Caleb held Molly’s solemn gaze.

“I don’t mean to sound patronizing but I need to know: you aren’t doing this to punish yourself or self-harm, are you?”

“No,” Caleb replied.  He had prepared for this, too.  “I want to hurt, but I am looking for more than pain.  Doing it myself would not have the same, ah….it has to be you, Mollymauk.”

“Thank you for being honest with me,” Molly said, the smile returning to his face.  “As long as you understand that I will not assist you in hurting yourself, I have a few ideas up my sleeve.”

Molly proceeded to show Caleb his collection of toys, letting Caleb familiarize himself with the ones he liked and demonstrating how they worked.  Caleb should not have been surprised by the wide array of equipment Molly had stashed under his bed, but how he managed to conceal and carry it all as they traveled remained a mystery.

Caleb was delighted to find that Molly had a flogger among the spread, just like drawing he had seen in a book that had caught his attention.  He turned it over in his hands, admired the fine leatherwork and experimented by whipping his own clothed knee with the heavy tresses.  Molly watched on with barely contained enthusiasm, vowing to make that night worthwhile for them both.

 

* * *

 

“Remind me, Caleb, what is your safe word?” Molly caressed Caleb’s cheek with the soft leather tresses, making Caleb shiver and raising goosebumps on his arms.

“Bugbear,” Caleb said instantly.  He had practiced, at Molly’s instruction, until the word felt comfortable on his lips.

“Good boy,” Molly cooed.  He dragged the tresses of the flogger over Caleb’s back, letting him know where he should expect to be hit.  The tassels cascaded over his sides and tickled his ribs before they were gone completely and Caleb waited in anticipation for the first strike.  He listened for movement beside him, but Molly kept still in the moments before he brought the flogger down on the upper right quadrant of Caleb’s back with a soft _thwack,_ drawing a gasp from the man’s lips.  

“Harder,” Caleb growled, impatiently.

“That isn’t how we ask for things,” Molly scolded, ghosting the tassels down Caleb’s spine.

“Please, Mollymauk, whip me harder,” Caleb begged.  “Please, I can take it.”

“I know you can, darling.”  Molly pressed a kiss to Caleb’s shoulder.  “All in due time.”

Molly continued to stroke at a crawling pace.  It took nearly ten excruciating minutes—Caleb was counting—of hitting the same spot again and again, increasing the pressure of the impact in small increments, before cresting the threshold that Caleb desired.  Molly lashed him on both sides of his back, and when Caleb would start leaning one way, he was hit from the other with a solid _smack_ that rung in his ears.

Caleb fisted his hands in the sheets, remembering to keep his elbows bent.  He concentrated until the hypnotic rhythm became all that there was.

Once on the left.  Three seconds.  One, two, three.

Once on the right.  Three seconds.  One, two, three.

Repeat, repeat, repeat, until the rest of the world fell away, leaving only bursts of dull pain that felt as if Molly was summoning something powerful from deep below to the surface.  That was when Caleb felt truly naked; he had been stripped of the suffocating responsibility to right his wrongs, to constantly walk the tightrope of morality.  He trusted, with all his soul, that Molly would take the broken pieces of the man he once was and make him whole again.

“Are you doing alright, Caleb?” Molly asked, cradling Caleb in the softness of his voice, way too sweet for a man holding a whip.

“ _Ja, noch einen, bitte_ ,” Caleb sobbed, unaware that he had slipped into Zemnian.  All of the stress that he had been holding inside bubbled over and came pouring from his eyes.

Caleb wondered how long he could stand the blissful torture, but the next strike never came.  Instead, Caleb jolted when a large hand squeezed his ass.  Molly dug his nails into the flesh before giving it a playful smack, almost sending Caleb pitching forward into the pillows.  He felt a trickle of cum drip down his thigh; his clit was hard and aching and he felt like every nerve that had been awakened by the flogger’s caress was on fire.

“You’re loving this, aren’t you, Caleb?” Molly purred, sliding a finger down the cleft off his ass, between the swollen lips of his vagina.  He swiped his now-slick finger over Caleb’s asshole, massaging the muscle but not yet prodding inside.  “Do you want to get off, now?”

“Oh, gods, yes, Mollymauk!” Caleb cried.  He lifted his ass up, but Molly instantly withdrew his hand and slapped it again.  He heard movement after a beat of silence and felt a pillow side under his thighs.

“Lie down, please,” Molly said, nudging Caleb’s ass forward.  His elbows gave out and he collapsed onto his stomach, unable to keep himself from humping the pillow in a shameless display of desperation.  Molly stilled him with a firm hand on his thigh.

“You’re doing so well, Caleb.  Let me take care of you.”

Caleb whimpered into the pillow.  His groin ached harder than his back at that point and he had barely been touched.  He felt the bed dip as Molly kneeled behind him and nudged his thighs apart.  Molly parted the cheeks with his hands, kissing each side before diving into the center.  Caleb moaned when Molly licked straight up the crack of his ass, hot and wet and powerful.  Molly dragged his tongue over Caleb’s asshole before finally, finally pressing the tip past the ring of muscle.  Caleb whimpered and clenched around Molly’s tongue, devastated when Molly drew back.

“You need to relax, love,” Molly said.  Caleb tried his best to comply, but he felt as if the connection between his brain and his body had been severed.  Molly tried again, probing deeper this time.  He reached around Caleb’s thigh, stroking between his lips and pinching his clit between two slick fingers.

Caleb tried to muffle his moans by biting the pillow under his head, salty with sweat and tears, but he nearly screamed when Molly withdrew and sank his teeth into the tender flesh of Caleb’s ass.

“None of that, now.  Let me hear you.”

Molly plunged his tongue back into Caleb’s asshole and and began thrusting in and out.  The hand between Caleb’s legs dipped two fingers inside his cunt, fucking Caleb with both his tongue and fingers with unrelenting force.  Molly curled his fingers and Caleb could not keep a desperate howl from tearing past his lips.

Caleb wanted to warn Molly, wanted to let him know he was close, but the words got stuck in his throat.  Molly’s fingers prodded rhythmically against his g-spot and Caleb could no longer keep his head up.  He wailed into the pillow as he came, his whole body shaking from the sudden release of energy from within.

Caleb was unsure how long it took for his body to stop shaking.  Time and space escaped him, and when he came down from the rush, his body had gone completely limp.  Molly’s tongue and fingers were gone and so was the blindfold as it was slipped off over his head. When his eyes adjusted to the light, he saw Molly resting his head on his arms on the mattress beside him.

“Welcome back,” Molly said.  His sweet smile made Caleb’s heart ache.  What had Caleb done to deserve this kind of attention?  How had Caleb, who had only done terrible things in his life, fall into the hands of someone so patient, so kind, so eager to prove that Caleb was worth his time and energy?  And most of all, how had Caleb disregarded every cautious second thought and let himself be carried away by the tornado of passion and vivid color that was Mollymauk Teleaf?

“Mollymauk,” Caleb felt, rather than heard, his own voice vibrating in his throat.  “Is this real?”

“Yes, this is real,” Molly confirmed, and to demonstrate, he brushed his knuckles against Caleb’s tear-stained cheek.  Caleb grabbed Molly’s wrist and pressed the palm to his face.

“Do you know where you are right now?”

“Mmm, the Leaky Tap,” muttered Caleb.  “In your room.  In Zadash.”

“That’s right.  I promise you, I’m real, you’re real, this is all real.”

Caleb’s mind was running on instinct, and that instinct trusted Molly’s every word.

Molly procured a waterskin from somewhere and pressed it to Caleb’s lips.  Caleb lifted his head just enough to drink, gulping down the entire thing as if he had not seen water for days.  He handed it back to Molly and collapsed again.

“I should go,” Caleb choked.  His throat constricted around the last syllable.  He wanted to cry but there were no tears left.  He could barely think, barely move.  He knew he would have to leave soon, so he was confused by the surprised look on Molly’s face.

“You’re in no condition to go anywhere, sweetheart,” Molly said, chuckling as if Caleb had told a joke.  He stroked Caleb’s hair and the man almost purred.  “I did quite a number on your back, so I’ll need to take care of it.  Is it alright if I get up for a moment? I won’t leave the room.”

Caleb nodded weakly.  He watched Molly rise and walk out of sight and return seconds later to sit on the edge of the bed.  He lathered his hands in the something from a bottle, a viscous liquid that smelled nice but unrecognizable to Caleb in his addled state.  He sucked in a breath when Molly began rubbing something cool into his shoulders that instantly eased his burning skin.  He melted under Molly’s fingers, the last of his tension disappearing and leaving him comfortably numb.

“I’m so glad I found you, Caleb Widogast,” Molly whispered after Caleb’s senses had dimmed beyond his own perception.  “You are a great man and a fantastic lover.  You make me want to be a better man myself, did you know that? You grant me the control that I desperately need; I feel grounded when I’m with you.  You are precious to me, Caleb.  I will take care of you for as long as you will let me.”

Caleb was not sure if he had heard it out loud or if Molly had somehow crept between the layers of his fading consciousness, but Caleb slept a dreamless sleep, swaddled in the sentiment that he was loved. 

**Author's Note:**

> If you have suggestions of things you'd like to see me write, or just want to yell at me about widomauk, hit me up or tumblr @keefling!


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